Ashland, OR Vacation Homes from ￥29,937

A deer on a road with vegetation on the sides.

Change your mind
Book hotels with free cancellation
Treat yourself
Sign in to save 10% or more on thousands of hotels
Sign in
Be picky
Search almost a million properties worldwide

Check prices for these dates

In two weeks

In two months

In three months

In four months

Our top choices for Ashland vacation homes

A bedroom with a large bed, a dresser, a mirror, a chandelier, and a staircase leading to another room.

1. Barclay Klum House by WanderLodges

Ashland

Melissa

￥42,839 total

includes taxes & fees

Sep 7 - Sep 8

A living room with a gray sofa, a brown leather chair, a round ottoman, a coffee table, and a large window with blinds.

2. East Main Downtown Bungalow

Historic Railroad District

Amy R.

￥34,603 total

includes taxes & fees

Oct 4 - Oct 5

A deck with a fire pit, outdoor seating, and a view of the countryside.

3. Grandview of Ashland

Ashland

Sonja

￥63,900 total

includes taxes & fees

Sep 13 - Sep 14

A staircase with wooden balusters, a round glass table with chairs, a patterned rug, and a white door with a decorative valance.

4. Savage Upon Siskiyou

Siskiyou-Hargadine Historic District

megan

￥65,792 total

includes taxes & fees

Sep 7 - Sep 8

A modern kitchen with wooden beams, a dining area with a rug, and a large island.

5. The Mountain Ave House by WanderLodges

Ashland

Joyce

￥53,781 total

includes taxes & fees

Sep 7 - Sep 8

A cozy living room with a built-in bench, a flat-screen TV, a bookshelf, and a vase of flowers.

6. Hanna's House by WanderLodges

Historic Railroad District

David

￥41,609 total

includes taxes & fees

Sep 10 - Sep 11

A cozy room with a bay window, a television, a bookshelf, and a vase of flowers.

7. Hanna`s House | Downtown Retreat, Steps to OSF

Historic Railroad District

Jim L.

￥48,094 total

includes taxes & fees

Sep 20 - Sep 21

A two-story house with a porch, a wooden fence, and a paved driveway.

8. Downtown Ashland House - Walk to Plaza and OSF!

Ashland

Jeff C.

￥60,534 total

includes taxes & fees

Sep 7 - Sep 8

A kitchen with white cabinetry, a black backsplash with star patterns, and two framed vintage Vogue magazine covers on the wall.

9. Swank Suites | King with Lux Tub

Historic Railroad District

Susie P.

￥29,937 total

includes taxes & fees

Oct 5 - Oct 6

A garden with a white fence, green hedges, and purple flowering trees.

10. Whimsy on B | The Studio

Historic Railroad District

￥34,768 total

includes taxes & fees

Sep 14 - Sep 15

A kitchen with granite countertops, dark cabinetry, and a refrigerator.

11. Quiet and peaceful cottage close to downtown

Siskiyou-Hargadine Historic District

Sue P.

￥51,695 total

includes taxes & fees

Oct 5 - Oct 6

A kitchen with white cabinets, a refrigerator, a stove, a microwave, and a sink.

12. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

Ashland

Matthew

￥74,755 total

includes taxes & fees

Sep 7 - Sep 8

A living room with a sofa, chairs, a coffee table, a TV, and a chandelier.

13. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

Ashland

Casey K.

￥52,046 total

includes taxes & fees

Sep 7 - Sep 8

14. Chateau Herb ~ Miranda Carriage House Apt

Ashland

"Loved loved loved staying here and had a fantastic stay with very reasonable rates! It is a bit difficult to find where the apartment was, but once we figured that part out, everything fell right into place. Huge thank you to the hosts for their excellent and timely communication- I also was a huge fan of the easy check in and check out process. Views are spectacular in this area and make for a really special and beautiful stay."

Cameron A.

￥42,923 total

includes taxes & fees

Sep 7 - Sep 8

A hallway with a blue wall, a framed welcome sign, a round mirror, and a table.

15. The Ashland Social | Main House

Ashland

Paul B.

￥88,726 total

includes taxes & fees

Sep 7 - Sep 8

A stone bridge over a stream with autumn leaves, surrounded by trees and a stone wall.

16. Charming house two blocks from downtown Ashland

Historic Railroad District

Julia W.

￥62,312 total

includes taxes & fees

Sep 13 - Sep 14

A residential property with a pathway leading to a house, surrounded by a wooden fence, and featuring a small patio area.

17. Come Stroll-inn in Downtown Ashland

Siskiyou-Hargadine Historic District

￥71,880 total

includes taxes & fees

Sep 7 - Sep 8

A bedroom with a large bed, a chandelier, a desk, a chair, and a window with curtains.

18. Moody Ashland Escape: Luxe Suite, Copper Tub

Historic Railroad District

Jon W.

￥45,254 total

includes taxes & fees

Sep 7 - Sep 8

A deck with a fire pit, seating, and a view of the mountains.

19. Hot tub | Sauna |Firepit |Sleeps 6!

Ashland

Heather K.

￥74,299 total

includes taxes & fees

Sep 13 - Sep 14

20. Whimsy on B | 2BR Steps to Downtown

Historic Railroad District

￥60,615 total

includes taxes & fees

Sep 7 - Sep 8

View all properties

Find vacation rentals that suit your style

Apartments

Condos

Save an average of 15% on thousands of hotels when you're signed in

Top Ashland Hotel Reviews

Prospero's Flagship Inn

10/10 Excellent

"Among all the 5–6 hotels we stayed at during our trip, this one stood out immediately. We booked a two‑queen bedroom, and it turned out to be exceptionally spacious — far larger and more comfortable than any of the other rooms we experienced. The layout felt open and relaxing, giving us plenty of room to unwind after long days of travel. The cleanliness, comfort, and thoughtful room design made a noticeable difference. It genuinely felt like a place where we could settle in rather than just pass through. Overall, a fantastic stay and easily one of the best accommodations on our trip."

Plaza Inn & Suites at Ashland Creek

10/10 Excellent

"The hotel was clean and most of the staff very helpful. We were located in a small, remote section of the hotel so umbrellas in the rooms would have been helpful to get to the main building where breakfast, ice & other amenities are located. At check out I asked for a receipt but was told that, since I booked through a third party, it would come from them. On this trip I booked 4 hotels through Hotels.com and all but this one provided a receipt. Seemed very unhelpful to me. If you are normally a walker it is an easy walk to the shops and many restaurants."

Timbers INN and Suites

10/10 Excellent

"Older but clean property. Being on special diets, my friend and I both appreciated booking a room with a kitchen (fridge, stove, plates, etc) A bit of a walk to OSF campus for those not used to walking, but doable for younger folks. Does appear to be on the bus line, but we had a car. A few smaller things weren't deal breakers (bigger coffee cups) but we did have major trouble, late at night, with the room key not working. Strongly suggested to mgmt that they replace all door knobs and locks."

Find out more about Ashland

Ashland Vacation Homes information

Number of reviews	469
Accommodation	273 Vacation Homes
Lowest Price	￥29,937
Highest Price	￥88,726

Explore a world of travel with Expedia

More ways to book

Book Vacation Homes in Ashland on Expedia.com

Room 1

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland vacation homes

1. Barclay Klum House by WanderLodges

2. East Main Downtown Bungalow

3. Grandview of Ashland

4. Savage Upon Siskiyou

5. The Mountain Ave House by WanderLodges

6. Hanna's House by WanderLodges

7. Hanna`s House | Downtown Retreat, Steps to OSF

8. Downtown Ashland House - Walk to Plaza and OSF!

9. Swank Suites | King with Lux Tub

10. Whimsy on B | The Studio

11. Quiet and peaceful cottage close to downtown

12. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

13. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

14. Chateau Herb ~ Miranda Carriage House Apt

15. The Ashland Social | Main House

16. Charming house two blocks from downtown Ashland

17. Come Stroll-inn in Downtown Ashland

18. Moody Ashland Escape: Luxe Suite, Copper Tub

19. Hot tub | Sauna |Firepit |Sleeps 6!

20. Whimsy on B | 2BR Steps to Downtown

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Prospero's Flagship Inn

Plaza Inn & Suites at Ashland Creek

Stratford Inn

The Bard's Inn, BW Signature Collection by Best Western

Comfort Inn & Suites Ashland

Callahan's Mountain Lodge

Ashland Springs Hotel

Lithia Springs Resort

Timbers INN and Suites

Find out more about Ashland

Ashland Vacation Homes information

Explore a world of travel with Expedia

Search Vacation Homes in Ashland

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Ashland vacation homes

1. Barclay Klum House by WanderLodges

2. East Main Downtown Bungalow

3. Grandview of Ashland

4. Savage Upon Siskiyou

5. The Mountain Ave House by WanderLodges

6. Hanna's House by WanderLodges

7. Hanna`s House | Downtown Retreat, Steps to OSF

8. Downtown Ashland House - Walk to Plaza and OSF!

9. Swank Suites | King with Lux Tub

10. Whimsy on B | The Studio

11. Quiet and peaceful cottage close to downtown

12. Historic Ohana House - Walk to Downtown Ashland, Hot Tub, Tiki Bar, Pet Friendly

13. Barclay Klum House | Walk to Downtown | Soaking Tub & Gourmet Kitchen

14. Chateau Herb ~ Miranda Carriage House Apt

15. The Ashland Social | Main House

16. Charming house two blocks from downtown Ashland

17. Come Stroll-inn in Downtown Ashland

18. Moody Ashland Escape: Luxe Suite, Copper Tub

19. Hot tub | Sauna |Firepit |Sleeps 6!

20. Whimsy on B | 2BR Steps to Downtown

Find vacation rentals that suit your style

Top Ashland Hotel Reviews

Prospero's Flagship Inn

Find out more about Ashland

Ashland Vacation Homes information

Explore a world of travel with Expedia